AU667129B2 - Injectable mesna solutions - Google Patents
Injectable mesna solutions Download PDFInfo
- Publication number
- AU667129B2 AU667129B2 AU48883/93A AU4888393A AU667129B2 AU 667129 B2 AU667129 B2 AU 667129B2 AU 48883/93 A AU48883/93 A AU 48883/93A AU 4888393 A AU4888393 A AU 4888393A AU 667129 B2 AU667129 B2 AU 667129B2
- Authority
- AU
- Australia
- Prior art keywords
- mesna
- solution
- injectable
- solutions
- stable
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/095—Sulfur, selenium, or tellurium compounds, e.g. thiols
- A61K31/105—Persulfides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/12—Mucolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cosmetics (AREA)
- Filling Or Discharging Of Gas Storage Vessels (AREA)
- Superconductors And Manufacturing Methods Therefor (AREA)
- Peptides Or Proteins (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Luminescent Compositions (AREA)
- Medical Preparation Storing Or Oral Administration Devices (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Abstract
Storage-stable mesna injection solutions with a pH above 7.5 and a preparation process are described.
Description
I A Injectable Mesna Solutions Description The chemical name of the active substance mesna is sodium-2-mercaptoethane sulfonate. (Formula I) S" HS-CH 2
-CH
2
-SO
3 Na Formula I Mesna for example protects the urinary organs in the treatment of tumour diseases with ifosfamide. In addition, mesna has already been used for a long time as a mucolytic agent.
Mesna is a white hygroscopic powder with a characteristic odour.
0 The substance is highly sensitive to oxidation and rapidly decomposes on contact with oxygen to form dimesna, particularly in a humid atmosphere. (Formula II) NaSO 3
-CH
2
-CH
2
-S-S-CH
2
-CH
2 -SO3Na Formula II Mesna has hitherto been applied orally, parenterally and by 1 means of inhalation. All the dosage forms used are liquid formulations that are given in the form of ampoules or drinkable ampoules. Since mesna is very sensitive to oxidation and reacts in the presence of oxygen to form dimesna, which is poorly absorbed, the aqueous solution has to be protected against oxygen. For this purpose the solution is sealed into glass ampoules.
The solution for parenteral application is offered in 2 ml, 4 ml and 10 ml ampoules containing 10 mesna.
Mesna is used to prevent urotoxic symptoms during ifosfamide therapy.
2 Mesna is generally given simultaneously with ifosfamide as well as after 4 and after 8 hours, in each case in a dose that corresponds to 20% of the ifosfamide dose, applied intravenously. The ifosfamide dose can be between lg/m 2 to 8g/m 2 body surface. The corresponding mesna doses consequently lie within a very broad spectrum. There was therefore a desire for multi-dose containers from which any quantity of injectable solution could be withdrawn and no wastage, such as incurred with opened ampoules, occurred.
These injection bottles were also intended to contain a larger volume of solution.
Deutsches Arzheibuch 9 (German Drug Book) requires that multi-dose containers be preserved to provide protection against microbial contamination. The injectable solution filled into ampoules is very stable. This formulation was therefore used and only one preservative, namely benzyl alcohol, used throughout the world for parenterally applied aqueous systems, was added thereto. The pH value of this solution is adjusted to 6.5 with sodium hydroxide solution. The solution also contains a complexing agent since mesna forms coloured complexes with heavy metal ions.
Stability storage tests showed, however, that these solutions were partially unstable.
The degradation product was identified as mesna acetal with benzaldehyde (Formula
III)
CH\ Formula III
/S-CH
2
-CH
2
-SO
3 Na *Benzaldehyde occurs in the formulation through oxidation of the benzyl alcohol used 20 as preservative.
:It has now surprisingly been found that this degradation product is only formed at S• pH values 7.5 and is not formed at a pH value of 7.5 According to a first embodiment of this invention there is provided an injectable mesna solution with a pH value of above 7.5 comprising mesna, one or more complexing 25 agents and one or more alkaline substances, and further comprising a preservative.
Included within this invention is the use of the injectable mesna solution according to the first embodiment for the prenaration of a medicament for preventing urotoxic side effects of oxazaphosphorin treatment.
Oxazaphosphorin is a generic term for a class of substances with cytostatic acting 30 alkylating agents. Belonging to it for instance are Ifosfamide, Trofosfamide and cyclophosphamid. The urotoxicity is caused by metabolic developed Acrolein that is a characteristic feature of this group of substances.
According to a another embodiment of this invention there is provided a method for preventing the side effect of oxazaphosphorin comprising administering to a patient who has taken oxazaphosphorin an effective amount of a stable injectable pharmaceutical composition with a pH value greater than 7.5, said composition comprising mesna, one or Smore complexing agents and one or more alkaline substances.
[N:\LIBFF]00282;SAK 3 The invention thus relates to an injectable solution which contains, to 1 part of mesna for example 0.00002 2.0 parts by weight preferably 0.0001 1.0 parts by weight in particular 0.0002 0.7 parts by weight of NaEDTA as complexing agent and for example 0.0002 2.0 parts by weight preferably 0.0003 1.7 parts by weight in particular 0.0004 1.4 parts by weight to of sodium hydroxide for pH adjustment and for example 0.001 30.0 parts by weight preferably 0.01 20.0 parts by weight in particular 0.018 12.0 parts by weight of benzyl alcohol as preservative.
i The amount by weight of mesna in an injectable solution of this type is generally 1 mg per ml to 540 mg/ml. The solutions can be applied directly i.v. or designed as infusion solutions or concentrates as supplements to infusions.
The appropriate volumes are between 0.5 ml and 100 ml. Water for injection purposes is used as solvent.
*999 999 9 .99.
9 ft* '*"*Jis In addition to the possible to use: complexing agents: above listed auxiliary substances it is also for example the calcium disodium salt of edetic acid, citric acid, tartaric acid or salts of orthophosphoric acid.
for example suitable to adjust the pH: sodium hydroxide, potassium hydroxide, tromethamine, sodium acetate, trisodium citrate, sodium monohydrogen phosphate, potassium monohydrogen phosphate.
The following are Preservatives: for example p-hydroxybenzoic acid ester, m-cresol, organomercuric compounds, chlorobutanol, quaternary ammonium compounds.
The preservatives may also be used in combination with benzyl alcohol.
To prepare the solution 80-90%, preferably 85% of the requisite amount of water (lacking in oxygen, i.e. the water may contain a maximum of 1.5ppm oxygen at 20°C) are prepared and sodium edetate, benzyl alcohol and mesna dissolved with stirring and constant nitrogen gassing. When dissolution is complete the pH is adjusted to 8.0 by adding 10N sodium hydroxide solution. This solution is made up to the final volume with water (lacking in oxygen).
The solution obtained in this manner is sterilised by filtration through conventional 15 pathogen-proof filters and then filled into appropriate containers for injectable preparations. The solution is covered with nitrogen during and after filtration. The storage time until filling into the injection containers, including the time to prepare the solution, should not exceed 4-5 hours.
For sterilisation purposes, conventional pathogen-proof filters, for example conventional bacteria filters with a pore size of 0.2 utm are used. The glass vessels used are previously sterilised in conventional manner. The injection water used must be sterile and pyrogen-free and meet the requirements of the Deutsches Arzneibuch 10, 1991 edition. The injection vessels used are appropriately those made of tubular glass or blowmoulded glass of hydrolytic class II (for example 10R, 30R, 50H), see in this connection Deutsches Arzneibuch 10, 1991 edition, VI.2.1. and DIN standards 58366 part 1 and part In addition, the injection vessels as well as additional C. o [N:\LIBxx]00776:KEH ill I r| 5 auxiliary substances, such as rubber stoppers and crimped caps, should meet the requirements of DIN standards 58366, part 2 and part 3, as well as 58367, part 1.
The volume of solution in the appropriate containers amounts per s container to between 4 ml and 100 ml, preferably between 10 ml and 75 ml, in particular between 40 ml and 60 ml. The amount of mesna per glass vessel is for example 4 mg to 50 g, preferably 1 g to 7.5 g, in particular 4 g 6 g.
After filling the solution under aseptic conditions, the bottles /0 are gassed with nitrogen to expel the oxygen and closed with injection stoppers. The filled injection bottles are sterilised in a steam steriliser.
The following examples illustrate the invention: Example 1 Injection bottle with 50 ml of a 10 injectable mesna solution Composition mesna (INN) 5000.0 mg benzyl alcohol 520.0 mg sodium edetate 12.5 mg sodium hydroxide 10.0 70.0 mg 1 2) Water for injection purposes 50.0 ml approx. 52.5 g- 1) Used to adjust the pH value and is therefore variable 2) Used as 10N sodium hydroxide solution 25-175 x 10 3 ml 3) 3) The use of more or less is balanced by water for injection purposes The density of the solution is 1.05 g/ml.
Preparation of the solution of the amount of water for injection purposes (lacking in oxygen) 6 are filled into a suitable vessel and the appropriate amounts of sodium edetate, benzyl alcohol and me:na dissolved therein with stirring and constant nitrogen gassing. The solution is adjusted.
to a pH value of 8.0 by addition of 10N sodium hydroxide solution and the result made up to the final volume with water for injection purposes (lacking in oxygen).
The water for injection purposes may contain a maximum of ppm oxygen at 20 0 C. pH value, density and refractive index (n 20 1.34-1.36) are determined as in-process controls.
1o The solution is sterilised by filtration using a 0.2 pm membrane filter. The solution is covered with nitrogen during and after filtration. A Sartorius SM 11107 or SM 11307 or Pall Filter NRP is, for example, used as a conventional pathogen-proof filter.
Particular and bacterial contamination is avoided during storage of the solution before filling. Storage at room temperature (200 22 0 C) should not exceed 4-5 hours. Additional conventional prefilters may also be used for purposes of sterile filtration (for example Sartorius SM 13400 or Pall LPA) to protect the S sterile filter.
R0 Cleaning the injection bottles DIN 50H/II, colourless 50 ml injection bottles are used as containers. They are flushed with hot and cold demineralised water and with air. All cleaning media are filtered to free them of suspended matter. To prevent recontamination due to particles from the air, the bottles are dried and sterilised using hot air (discontinuously at 180°C, 2 hours, continuous at 350 0 C for minutes).
The rubber stoppers (for example Helvoet FM 157/1 grey) used tc close the injection bottles are cleaned using demineralised 0o water and, for example, a cleaning agent consisting of non-ionogenic surfactants and phosphoric acid esters in aqueou-s solution (for example MB 70, Huber, Freiburg).
The cleaned stoppers are rinsed free of fibres and fluff using water for injection purposes or filtered demineralised water.
k It 7 The stoppers cleaned in this manner are then sterilised using steam.
The injection bottles cleaned and sterilised in this manner are then gassed aseptically with nitrogen to displace the oxygen in T the air, filled with 52 ml mesna solution and gassed again.
Finally, the stoppers are positioned and secured with crimped caps. The filling volume is statistically monitored by then weighing the contents. The nominal filling amount is 52 ml 54.6 g. The residual oxygen content in the headspace of the /0 injection bottle is also monitored.
The filled injection bottles are sterilised in a steam steriliser (at least 1200 20 minutes).
The injection bottles are checked for incorrect closure, outer faults, clarity and particulate impurities.
*0 /6 Example 2 0 Injection bottle with 50 ml of a 50 concentrate for addition to infusion solutions: Composition: mesna 25,000 g benzyl alcohol 0.520 g Na EDTA 0.0125 g sodium hydroxide 0.05 0.35 g water for injection purposes ad 50,000 ml 61.0 g 0 The density of the concentrate is 1.22 g/ml 20 0 C. The preparation and sterile filtration of the solution, cleaning and neo.
sterilisation of the bottles and rubber stoppers, filling, closing of the bottles and final sterilisation are carried out according to Example 1.
Claims (4)
1. A stable, injectable pharmaceutical composition with a pH value of above comprising mesna, one or more complexing agents and one or more alkaline substances and further comprising a preservative.
2. The composition of claim 1 wherein the pH is 7.5 to
3. A stable, injectable pharmaceutical composition substantially as hereinbefore described with reference to any one of the Examples.
4. A method for preventing the side effect of oxazaphosphorin comprising administering to a patient who has taken oxazaphosphorin an effective amount of a stable injectable pharmaceutical composition with a pH value greater than 7.5, said composition comprising mesna, one or more complexing agents and one or more alkaline substances. Dated 10 January, 1996 ASTA Medica Aktiengesellschaft Patent Attorneys for the Applicant/Nominated Person SPRUSON FERGUSON .o g S* a ea a e a *o*oo o *eo [N:\LIBFF]00282:SAK Injectable Mesna Solutions Abstract The invention provides storage-stable injectable solutions of mesna, sodium-2- mercaptoethane sulfonate of the formula HS-CH1 2 -CH 2 -SO 3 Na Formula I. The solutions have a pH value higher than 7.5. They are useful for preventing the side effect of oxazaphosphorin. IN:'L11U101457:GA
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4233842 | 1992-10-08 | ||
DE4233842A DE4233842A1 (en) | 1992-10-08 | 1992-10-08 | Mesna injection solutions |
Publications (2)
Publication Number | Publication Date |
---|---|
AU4888393A AU4888393A (en) | 1994-04-21 |
AU667129B2 true AU667129B2 (en) | 1996-03-07 |
Family
ID=6469925
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU48883/93A Expired AU667129B2 (en) | 1992-10-08 | 1993-10-07 | Injectable mesna solutions |
Country Status (28)
Country | Link |
---|---|
US (2) | US5728738A (en) |
EP (1) | EP0591710B1 (en) |
JP (1) | JP3636372B2 (en) |
KR (1) | KR100364466B1 (en) |
CN (1) | CN1071114C (en) |
AT (1) | ATE139693T1 (en) |
AU (1) | AU667129B2 (en) |
BR (1) | BR9304151A (en) |
CA (1) | CA2107961C (en) |
CZ (1) | CZ284584B6 (en) |
DE (2) | DE4233842A1 (en) |
DK (1) | DK0591710T3 (en) |
EG (1) | EG20308A (en) |
ES (1) | ES2089661T3 (en) |
FI (1) | FI111804B (en) |
GR (1) | GR3020669T3 (en) |
HK (1) | HK7397A (en) |
HR (1) | HRP931267B1 (en) |
HU (1) | HU217123B (en) |
IL (1) | IL107187A (en) |
NO (1) | NO303712B1 (en) |
NZ (1) | NZ248873A (en) |
RU (1) | RU2105550C1 (en) |
SI (1) | SI9300525A (en) |
SK (1) | SK279609B6 (en) |
TW (1) | TW279131B (en) |
UA (1) | UA26134C2 (en) |
ZA (1) | ZA937458B (en) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6828415B2 (en) | 1993-02-19 | 2004-12-07 | Zentaris Gmbh | Oligopeptide lyophilisate, their preparation and use |
IT1284973B1 (en) * | 1996-10-11 | 1998-05-28 | A R D O Associazione Ricerca E | USE OF SODIUM 2-MERCAPTOETHANE SULFONATE (MESNA) IN SURGERY |
US6031006A (en) * | 1999-10-21 | 2000-02-29 | Bionumerik Pharmaceuticals, Inc. | Method of treating diabetic nephropathy |
TW201036529A (en) | 2009-03-25 | 2010-10-01 | Askey Computer Corp | A liquid crystal anti-freeze method and a liquid crystal module using the liquid crystal anti-freeze method |
UA74097U (en) * | 2012-07-24 | 2012-10-10 | Николай Иванович Гуменюк | Method for manufacturing drug for treatment of tuberculosis |
EP3597128A1 (en) | 2013-05-07 | 2020-01-22 | AuXin Surgery SA | Device for chemically assisted dissection |
BE1024110B1 (en) * | 2016-10-18 | 2017-11-16 | Auxin Surgery Sa | Chemical assisted dissection device, method and formulation |
US20200289144A1 (en) | 2016-03-14 | 2020-09-17 | Auxin Surgery Sa | Device, method and formulation for chemically assisted dissection |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3111770A1 (en) * | 1981-03-25 | 1982-10-07 | Heyl Chemisch-pharmazeutische Fabrik GmbH & Co KG, 1000 Berlin | USE OF DIMERCAPTOPROPANESULPHONIC ACID AND DIMERCAPTOSEMBER ACID FOR THE PRODUCTION OF PHARMACEUTICAL AGENTS |
IT1185551B (en) * | 1985-04-15 | 1987-11-12 | Schering Spa | PHARMACEUTICAL COMPOSITIONS BASED ON MERCAPTOETHANE SULPHONE ACID WITH THERAPEUTIC ACTIVITY, ORGANIC SALINE DERIVATIVES OF MERCAPTO ETHAN SULPHONIC ACID USEFUL FOR SUCH COMPOSITIONS AND RELATED PREPARATION PROCEDURE |
ES2040394T3 (en) * | 1988-03-19 | 1993-10-16 | Asta Medica Aktiengesellschaft | PROCEDURE FOR PREPARING A LYOPHILIZED MATERIAL OF IFOSFAMIDE AND MESNA. |
-
1992
- 1992-10-08 DE DE4233842A patent/DE4233842A1/en not_active Withdrawn
-
1993
- 1993-08-24 TW TW082106854A patent/TW279131B/zh not_active IP Right Cessation
- 1993-09-13 DK DK93114670.8T patent/DK0591710T3/en active
- 1993-09-13 AT AT93114670T patent/ATE139693T1/en active
- 1993-09-13 EP EP93114670A patent/EP0591710B1/en not_active Expired - Lifetime
- 1993-09-13 DE DE59303067T patent/DE59303067D1/en not_active Expired - Lifetime
- 1993-09-13 ES ES93114670T patent/ES2089661T3/en not_active Expired - Lifetime
- 1993-10-03 EG EG64293A patent/EG20308A/en active
- 1993-10-05 SI SI9300525A patent/SI9300525A/en unknown
- 1993-10-05 CN CN93118643A patent/CN1071114C/en not_active Expired - Lifetime
- 1993-10-05 IL IL10718793A patent/IL107187A/en not_active IP Right Cessation
- 1993-10-06 KR KR1019930020576A patent/KR100364466B1/en not_active IP Right Cessation
- 1993-10-06 NZ NZ248873A patent/NZ248873A/en not_active IP Right Cessation
- 1993-10-06 UA UA93002240A patent/UA26134C2/en unknown
- 1993-10-06 BR BR9304151A patent/BR9304151A/en not_active Application Discontinuation
- 1993-10-06 JP JP25042793A patent/JP3636372B2/en not_active Expired - Lifetime
- 1993-10-07 ZA ZA937458A patent/ZA937458B/en unknown
- 1993-10-07 SK SK1079-93A patent/SK279609B6/en not_active IP Right Cessation
- 1993-10-07 AU AU48883/93A patent/AU667129B2/en not_active Expired
- 1993-10-07 HR HRP4233842.5A patent/HRP931267B1/en not_active IP Right Cessation
- 1993-10-07 NO NO933590A patent/NO303712B1/en not_active IP Right Cessation
- 1993-10-07 CZ CZ932097A patent/CZ284584B6/en not_active IP Right Cessation
- 1993-10-07 HU HU9302837A patent/HU217123B/en unknown
- 1993-10-07 FI FI934410A patent/FI111804B/en not_active IP Right Cessation
- 1993-10-07 RU RU93048160A patent/RU2105550C1/en active
- 1993-10-07 CA CA002107961A patent/CA2107961C/en not_active Expired - Fee Related
-
1995
- 1995-06-07 US US08/474,246 patent/US5728738A/en not_active Expired - Lifetime
-
1996
- 1996-04-23 US US08/636,821 patent/US5696172A/en not_active Expired - Lifetime
- 1996-07-31 GR GR960402027T patent/GR3020669T3/en unknown
-
1997
- 1997-01-16 HK HK7397A patent/HK7397A/en not_active IP Right Cessation
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